Sodium borohydride → HCID 135730597, compound

HRID 354207Notes

Reaction equation

HRID 354207 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:7]=[C:8]([C:17]2[NH:18][C:19](=[O:37])[C:20]3[C:21](=[C:23]([CH2:35][CH3:36])[N:24]([CH:26]4[CH2:31][CH2:30][N:29]([C:32](=[O:34])[CH3:33])[CH2:28][CH2:27]4)[N:25]=3)[N:22]=2)[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][CH:11]=1)(=[O:5])[CH3:4]>CO>[C:32]([N:29]1[CH2:28][CH2:27][CH:26]([N:24]2[C:23]([CH2:35][CH3:36])=[C:21]3[N:22]=[C:17]([C:8]4[C:9]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[N:10][CH:11]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:7]=4)[NH:18][C:19](=[O:37])[C:20]3=[N:25]2)[CH2:31][CH2:30]1)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 135730607HCID 135730607, compound

Product 1

HCID 135730597HCID 135730597, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (6 mg, 0.15 mmol) was added to a suspension of the title compound from example 131 (140 mg, 0.3 mmol) in dry methanol (3 ml) at 0° C. under nitrogen. After 30 min the solvent was removed in vacuo, and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated, and the aqueous layer was extracted further with ethyl acetate (2×20 ml). Combined organic layers were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (98:2 to 95:5 methylene chloride:methanol as eluent) to yield the title compound as a white foam (120 mg, 0.25 mmol).

Workup

  1. customAfter 30 min the solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted further with ethyl acetate (2×20 ml)
  5. washCombined organic layers were washed with brine (20 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash column chromatography (98:2 to 95:5 methylene chloride:methanol as eluent)

Sources & evidence

ORD record
ord-13f9931c04894a519b2bdc183bf626fc
Source dataset
uspto-grants-2004_06
Patent number
US06756373B1

Reaction notes

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